Generations in Dialogue: Bridging Perspectives in AI is a podcast from AAAI featuring thought-provoking discussions between AI experts, practitioners, and enthusiasts from different age groups and backgrounds. Each episode delves into how generational experiences shape views on AI, exploring the challenges, opportunities, and ethical considerations that come with the advancement of this transformative technology. In the second episode of this new series from AAAI, host Ella Lan chats to Professor Andreea Bobu about choosing her research direction, working with humans in-the-loop, things to consider when working with data, system design challenges, the gap between what we think we're programming and what we've actually programmed, privacy and personalisation, and advice for early-career researchers interested in human-centric AI. Andreea Bobu is an Assistant Professor at MIT and leads the Collaborative Learning and Autonomy Research (CLEAR) Lab, where she develops autonomous agents that learn to act for, with, and around people. Her research focuses on aligning robot behavior with human expectations by studying how agents can acquire the right supervision--whether from direct human input or priors--build shared task representations with users, and address misalignment from differing human models.